Address
416 Fleming Street, Key West, FL
Price
$ 3,500,000
Property Attributes
- MLS#620434
- TypeSingle Family
- Listing Status Active
- CountyMONROE
- CityKey West
- AreaKey West
- NeighborhoodOld Town - Unlisted
- Zip33040
- StyleMulti-Units
- Year Built1938
- Taxes$ 19952
- Price$ 3,500,000
- Bedrooms5
- Full Bathrooms4
- Half Bathrooms1
- Sqr Footage2575
- Lot Size0.15 Acres
Data Source:
Florida Keys MLS (FLKMLS)
Property Description
First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's most iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches,timeless architectural details, and an unbeatable Old Town location.Originally renovated in 2001 and thoughtfully updated through 2025, the property blends historic character with modern functionality.. Situated on a generous 6,700-square-foot lot, the property offers parking for up to nine vehicles--an exceptional amenity in Old Town Key West--with ample space remaining for the addition of a private pool. Enjoy picturesque views of the surrounding historic district from the expansive porches while embracing the relaxed island atmosphere that defines Key West living. A unique and valuable feature of the property is its 15,000-gallon underground rainwater harvesting cistern, measuring approximately 11' x 13' x 19'. Designed and constructed by a retired Boeing piping engineer, the system incorporates a dual-chamber design, allowing one chamber to remain in service while the other is isolated for inspection, cleaning, and maintenance. The home's roof drainage system has been professionally plumbed to collect and direct rainwater into the cistern, with a diverter valve that allows water to be routed either into storage or discharged into the yard. With the addition of a pump, this impressive system can be reactivated for irrigation and other sustainable water-management uses.Offering historic significance, income potential, abundant parking, modern updates, and a truly rare engineering feature, this exceptional property is a one-of-a-kind opportunity in the heart of Old Town.Corner Lane Lot: dimensions 50' x 134 Bike Rack Stays!
| Price History | |
|---|---|
| 6/28/2026 | Listed $3,500,000 |
General Features
| Living Area | 2575.00 |
|---|---|
| Construction | Frame,Other |
| Utilities | FKAA,Elect Separate Meter,Cistern,Well |
| Roof | Metal Roof |
| Appliances | Dryer,Microwave,Oven,Refrigerator,Dishwasher |
| Flood Zone | X |
| Zoning | HRO - Historic Residential/Office |
| HOA Fee | 0.00 |
| Pets Allowed Y/N | Pets Allowed |
| Status | Active |
| Full Baths | 4 |
| Half Baths | 1 |
| Year Built | 1938 |
| Subdivision | Old Town - Unlisted (1.0) |
| Style | Multi-Units |
| View | No Waterview |
| Property Type | A |
| Floor Number | 3.00 |
| Neighborhood Feature | Other Area Features |
| Fee Includes | Other |
| Acres | 0.15 |
| Lot Sqft | 6700.00 |
| Rental Allowed | Yes |
| Accessibility Features | Grab Bars,Wheelchair Ramp,Parking |
| Building Style: Above Flood | Yes |
| Building Style: Stories | 3 Stories |
| Dockage | None |
| KW Neighborhood | Old Town-S of Truman |
| Min Rental Days | 28.00 |
| License Info | Non Trans Rntl Lic |
Interior Features
| Interior Amenities | Drapes/Blinds Incl,Pull Down Stairs,Built-in Cabinets,Storage,Smoke Alarms,Lobby,Granite Counter Top,Entrance Foyer,Cathedral Ceilings |
|---|---|
| Total Units | 0.00 |
| Furnished Y/N | Unfurnished |
| Flooring | Tile,Wood |
Exterior Features
| Exterior Amenities | Storage |
|---|---|
| Pool | No |
| Waterfront | None |
| Lot Size | 50 X 134 |
| Land Size | Less Than 1/4 Acre |
| Porch/Balcony | Open Porch/Balcony,Deck,Patio |
| Public Sewer Hookup | Yes |
| Shutters | Panel |
| Side | Median |
| Vehicle Storage | Off Street Parking |
| Vehicle Storage: Car(s) | 4+ |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 33040
Price
Taxes
Year Built
Visits
In The Neighborhood
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- 1,281 SqFt
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516 Elizabeth Street
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- Size
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$ 1,395,000
709 Olivia Street
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- Type
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- Size
- 1,092 SqFt
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$ 6,750,000
411 Louisa Street
Key West, FL 33040
- Type
- Single Family
- Size
- 3,663 SqFt
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- 5 Beds + 4.5 Baths
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$ 999,000
506 Grinnell Street
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- Type
- Single Family
- Size
- 1,416 SqFt
- Rooms
- 3 Beds + 1.5 Baths
Reduced
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$ 3,495,000
710 Caroline Street
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- Type
- Single Family
- Size
- 2,250 SqFt
- Rooms
- 4 Beds + 4.5 Baths
Key West
$ 3,300,000
214 Eanes Lane
Key West, FL 33040
- Type
- Single Family
- Size
- 2,573 SqFt
- Rooms
- 4 Beds + 3.5 Baths
Reduced
Key West
$ 2,249,000
1109 Stump Lane
Key West, FL 33040
- Type
- Single Family
- Size
- 1,724 SqFt
- Rooms
- 3 Beds + 3 Baths
Reduced
Key West
$ 2,395,000
319 Grinnell Street
Key West, FL 33040
- Type
- Single Family
- Size
- 1,456 SqFt
- Rooms
- 3 Beds + 2 Baths
Reduced
Key West
$ 949,000
818 Elizabeth Street, # Front
Key West, FL 33040
- Type
- Single Family
- Size
- 1,520 SqFt
- Rooms
- 3 Beds + 3 Baths
Reduced
Key West
$ 3,750,000
919-921 Thomas Street
Key West, FL 33040
- Type
- Single Family
- Size
- 3,015 SqFt
- Rooms
- 7 Beds + 7.5 Baths
New Construction
Key West
$ 2,033,000
1 & 2 Aronovitz Lane
Key West, FL 33040
- Type
- Single Family
- Size
- 888 SqFt
- Rooms
- 2 Beds + 1 Baths
Information is deemed to be reliable, but is not guaranteed. © 2026 MLS and FBS. Prepared by Florida Keys MLS, Inc. on September 11, 2026 7:48 AM UTC The information on this sheet has been made available by the MLS and may not be the listing of the provider. The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information
